GB1379188A - Quinazoline compounds and processes for their production - Google Patents
Quinazoline compounds and processes for their productionInfo
- Publication number
- GB1379188A GB1379188A GB3932673A GB3932673A GB1379188A GB 1379188 A GB1379188 A GB 1379188A GB 3932673 A GB3932673 A GB 3932673A GB 3932673 A GB3932673 A GB 3932673A GB 1379188 A GB1379188 A GB 1379188A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- reacted
- compounds
- product
- alkylthiophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1379188 Quinazoline derivatives PARKE DAVIS & CO 20 Aug 1973 [21 Aug 1972] 39326/73 Heading C2 The invention comprises compounds of formula or acid addition salts thereof; wherein R<SP>1</SP> represents -C 2 H 5 , or an n- or iso-propyl group; R<SP>2</SP> represents H or -CH 3 ; n represents 4, 5 or 6; and each of X and Y represents H or -OCH 3 . These compounds may be obtained by reacting an o-aminobenzamide of formula with phosgene. The starting material (B) may be prepared by the following sequence of reactions: 1-(o-alkylthiophenyl piperazine of formula is reacted with a bromonitrile of formula Br-(CH 2 ) n-1 -CN in the presence of K 2 CO 3 and the product reduced with LiAlH 4 followed by hydrolysis to give 1-(aminoalkyl)-4-(o-alkylthiophenyl)piperazine of formula The product D is reacted with an isatoic anhydride of formula to produce an o-aminobenzamide of Formula B. According to another sequence of reactions a benzoic acid derivative of formula is converted to the acid chloride by reaction with thionyl chloride, and the acid chloride is reacted with a compound of Formula (D), and the reaction product is treated with a base to produce an o-nitrobenzamide of formula This compound is reduced to form an amide of Formula (B) The compounds according to the invention are reported to have central nervous system depressant activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00282332A US3819630A (en) | 1972-08-21 | 1972-08-21 | 3-(1-piperazinylalkyl)-2,4-quinazolinedione compounds and methods for their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1379188A true GB1379188A (en) | 1975-01-02 |
Family
ID=23081024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3932673A Expired GB1379188A (en) | 1972-08-21 | 1973-08-20 | Quinazoline compounds and processes for their production |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3819630A (en) |
| JP (1) | JPS4985077A (en) |
| AR (1) | AR200736A1 (en) |
| AT (1) | AT327923B (en) |
| AU (1) | AU476177B2 (en) |
| BE (1) | BE803800A (en) |
| CA (1) | CA990293A (en) |
| CH (1) | CH586695A5 (en) |
| DE (1) | DE2342028A1 (en) |
| DK (1) | DK132758C (en) |
| ES (1) | ES418036A1 (en) |
| FI (1) | FI57937C (en) |
| FR (1) | FR2196803B1 (en) |
| GB (1) | GB1379188A (en) |
| IE (1) | IE38102B1 (en) |
| IL (1) | IL43033A (en) |
| NL (1) | NL7311458A (en) |
| NO (1) | NO138660C (en) |
| PH (1) | PH9220A (en) |
| SE (1) | SE398120B (en) |
| ZA (1) | ZA735728B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040793A1 (en) * | 1980-05-22 | 1981-12-02 | Masayuki Ishikawa | Novel quinazoline-dione compounds, process for production thereof and pharmaceutical use thereof |
| EP0104614A1 (en) * | 1982-09-24 | 1984-04-04 | Chugai Seiyaku Kabushiki Kaisha | Phenylpiperazine derivatives and process for producing the same |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879395A (en) * | 1973-10-23 | 1975-04-22 | Parke Davis & Co | 3-(1-Piperazinylalkylamino)-2-cycloalken-1-one compounds and methods for their production |
| US4268511A (en) * | 1980-03-11 | 1981-05-19 | Berri-Balzac | 3-Amino(1H,3H)quinazoline-2,4-dione derivatives and their therapeutic applications |
| JPS58159480A (en) * | 1982-03-17 | 1983-09-21 | Chugai Pharmaceut Co Ltd | Novel phenylpiperazine derivative |
| JPS60169467A (en) * | 1984-02-10 | 1985-09-02 | Chugai Pharmaceut Co Ltd | Novel phenylpiperazine derivative |
| US4711883A (en) * | 1985-09-30 | 1987-12-08 | Ortho Pharmaceutical Corporation | Substituted 3-(4-phenyl-1-piperazinyl)alkylquinazolin-2,4-(1H,3H) diones, methods of preparation, compositions and method of use |
| US5160727A (en) * | 1990-02-13 | 1992-11-03 | Warner-Lambert Company | Tumor cell sensitization method using quinazolinedione derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274194A (en) * | 1963-03-29 | 1966-09-20 | Miles Lab | Quinazolinedione derivatives |
-
1972
- 1972-08-21 US US00282332A patent/US3819630A/en not_active Expired - Lifetime
-
1973
- 1973-08-20 GB GB3932673A patent/GB1379188A/en not_active Expired
- 1973-08-20 ES ES418036A patent/ES418036A1/en not_active Expired
- 1973-08-20 DK DK457173A patent/DK132758C/en active
- 1973-08-20 AR AR249617A patent/AR200736A1/en active
- 1973-08-20 AU AU59420/73A patent/AU476177B2/en not_active Expired
- 1973-08-20 CH CH1194973A patent/CH586695A5/xx not_active IP Right Cessation
- 1973-08-20 SE SE7311297A patent/SE398120B/en unknown
- 1973-08-20 JP JP48093222A patent/JPS4985077A/ja active Pending
- 1973-08-20 IE IE1437/73A patent/IE38102B1/en unknown
- 1973-08-20 NO NO3283/73A patent/NO138660C/en unknown
- 1973-08-20 DE DE19732342028 patent/DE2342028A1/en not_active Withdrawn
- 1973-08-20 NL NL7311458A patent/NL7311458A/xx not_active Application Discontinuation
- 1973-08-20 CA CA179,161A patent/CA990293A/en not_active Expired
- 1973-08-20 AT AT722773A patent/AT327923B/en not_active IP Right Cessation
- 1973-08-20 FI FI2591/73A patent/FI57937C/en active
- 1973-08-20 FR FR7330161A patent/FR2196803B1/fr not_active Expired
- 1973-08-20 IL IL43033A patent/IL43033A/en unknown
- 1973-08-20 BE BE134748A patent/BE803800A/en unknown
- 1973-08-21 ZA ZA00735728A patent/ZA735728B/en unknown
- 1973-09-26 PH PH15053*UA patent/PH9220A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040793A1 (en) * | 1980-05-22 | 1981-12-02 | Masayuki Ishikawa | Novel quinazoline-dione compounds, process for production thereof and pharmaceutical use thereof |
| EP0104614A1 (en) * | 1982-09-24 | 1984-04-04 | Chugai Seiyaku Kabushiki Kaisha | Phenylpiperazine derivatives and process for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| AR200736A1 (en) | 1974-12-13 |
| FI57937C (en) | 1980-11-10 |
| AT327923B (en) | 1976-02-25 |
| FR2196803B1 (en) | 1976-05-14 |
| ES418036A1 (en) | 1976-03-01 |
| DK132758C (en) | 1976-08-23 |
| AU5942073A (en) | 1975-02-20 |
| NL7311458A (en) | 1974-02-25 |
| DE2342028A1 (en) | 1974-03-07 |
| AU476177B2 (en) | 1976-09-16 |
| PH9220A (en) | 1975-07-10 |
| DK132758B (en) | 1976-02-02 |
| FR2196803A1 (en) | 1974-03-22 |
| CA990293A (en) | 1976-06-01 |
| IL43033A (en) | 1976-09-30 |
| ATA722773A (en) | 1975-05-15 |
| US3819630A (en) | 1974-06-25 |
| IL43033A0 (en) | 1973-11-28 |
| JPS4985077A (en) | 1974-08-15 |
| FI57937B (en) | 1980-07-31 |
| IE38102B1 (en) | 1977-12-21 |
| CH586695A5 (en) | 1977-04-15 |
| NO138660C (en) | 1978-10-18 |
| BE803800A (en) | 1973-12-17 |
| IE38102L (en) | 1974-02-21 |
| NO138660B (en) | 1978-07-10 |
| ZA735728B (en) | 1975-04-30 |
| SE398120B (en) | 1977-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |